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Puerto Rico Cruises Starting In October 2026 and 2027

If you're looking at joining a cruise to Puerto Rico in October 2026 or 2027, we have 26 unique cruise itineraries and 134 departures available, operated by seven of the world's leading cruise lines departing in October.
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26 Cruises (134 Cruise Departures)
13 Day Halloween Transatlantic from Spain with Virgin Voyages
Cruise
 (1)

13 Days (12 Nights) Barcelona to San Juan
Cruise Line: Virgin Voyages
Ship: Scarlet Lady
Departure: 31 October 2027
Visit: Spain, Morocco, Puerto Rico
Limited Time Offer
Inside
$1,145
Oceanview
$1,202
Balcony
$1,314
Suite
$4,610
From
US$1,145
Per Person
View Trip
15 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

15 Days (14 Nights) Barcelona to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 31 October 2026
Visit: Spain, Portugal, Puerto Rico, USA
Inside
$766
Oceanview
$965
Balcony
$1,184
Suite
$3,184
From
US$766
Per Person
View Trip
8 Day Eastern Caribbean with St. Kitts with Princess
Cruise
 (6)

8 Days (7 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ships: Island Princess, Sky Princess
Departures: Oct 2027 to Feb 2028
Visit: USA, Dominican Republic, Puerto Rico, Saint Kitts and Nevis
Princess Standard
Inside
$584
Oceanview
$634
Balcony
$709
Suite
$1,289
From
US$584
Per Person
View Trip
16 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

16 Days (15 Nights) Palma de Mallorca to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 October 2026
Visit: Spain, Portugal, Puerto Rico, USA
Inside
$836
Oceanview
$1,065
Balcony
$1,265
Suite
$2,698
From
US$836
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ship: Icon Of The Seas
Departures: Jun 2026 to Oct 2026
Visit: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$1,527
Oceanview
$1,800
Balcony
$2,089
Suite
$2,825
From
US$1,527
Save 836
Per Person
View Trip
14 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

14 Days (13 Nights) Barcelona to Miami
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 31 October 2026
Visit: Spain, Portugal, Puerto Rico, USA
Inside
$708
Oceanview
$894
Balcony
$1,100
Suite
-
From
US$708
Per Person
View Trip
8 Day Perfect Day Cococay & East Caribbean with Royal Caribbean
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Star Of The Seas
Departures: May 2026 to Oct 2027
Visit: USA, Bahamas, Puerto Rico, Saint Martin
Bonus Onboard Credit
Exclusive Savings
Inside
$1,221
Oceanview
$1,486
Balcony
$1,646
Suite
$2,880
From
US$1,315
Save 930
Per Person
View Trip
9 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

9 Days (8 Nights) Orlando to Orlando
Cruise Line: Royal Caribbean
Ship: Adventure of the Seas
Departures: Sep 2026 to Oct 2026
Visit: USA, Virgin Islands, Puerto Rico, Bahamas
Exclusive Savings
Inside
$715
Oceanview
$953
Balcony
$1,286
Suite
$2,615
From
US$715
Save 487
Per Person
View Trip
14 Day West Indies to Spain with Viking Cruises
Cruise
 (5)

14 Days (13 Nights) Barcelona to San Juan
Cruise Line: Viking Cruises
Ship: Viking Sea
Departure: 23 October 2026
Visit: Spain, Portugal, Sint Maarten, Puerto Rico
Viking $999 Air Deal
Exclusive Savings
Inside
-
Oceanview
-
Balcony
$3,299
Suite
$5,999
From
US$3,299
Save 200
Per Person
View Trip
8 Day Eastern Caribbean with Puerto Rico with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: Jul 2026 to Oct 2026
Visit: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$481
Oceanview
$501
Balcony
$726
Suite
$971
From
US$481
Per Person
View Trip
8 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: Royal Caribbean
Ships: Allure of the Seas, Symphony of the Seas
Departures: Apr 2026 to Oct 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$916
Oceanview
$994
Balcony
$1,143
Suite
$3,059
From
US$916
Save 517
Per Person
View Trip
8 Day Caribbean And Antilles with MSC Cruises
Cruise

8 Days (7 Nights) Miami to Miami
Cruise Line: MSC Cruises
Ship: MSC World America
Departures: Apr 2026 to Mar 2028
Visit: USA, Dominican Republic, Puerto Rico, Bahamas
Inside
$584
Oceanview
$814
Balcony
$934
Suite
$1,274
From
US$584
Per Person
View Trip
10 Day Eastern Caribbean & Perfect Day with Royal Caribbean
Cruise

10 Days (9 Nights) New York to New York
Cruise Line: Royal Caribbean
Ship: Oasis of the Seas
Departure: 25 October 2026
Visit: USA, Bahamas, Puerto Rico, Dominican Republic
Exclusive Savings
Inside
$1,204
Oceanview
$1,667
Balcony
$1,477
Suite
$3,044
From
US$1,204
Save 612
Per Person
View Trip
16 Day Caribbean And Antilles with MSC Cruises
Cruise
 (1)

16 Days (15 Nights) Orlando to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 30 October 2027
Visit: USA, Bahamas, Mexico, Dominican Republic, Puerto Rico
Inside
$1,359
Oceanview
$1,559
Balcony
$1,919
Suite
$3,489
From
US$1,359
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ship: Rhapsody of the Seas
Departures: Sep 2026 to Oct 2026
Visit: Puerto Rico, Virgin Islands, Saint Martin, Antigua and Barbuda, Dominica
Exclusive Savings
Inside
$715
Oceanview
$633
Balcony
$1,257
Suite
$1,323
From
US$633
Save 510
Per Person
View Trip
17 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

17 Days (16 Nights) Rome to Miami
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 28 October 2026
Visit: Italy, Spain, Portugal, Puerto Rico, USA
Inside
$888
Oceanview
$1,131
Balcony
$1,346
Suite
-
From
US$888
Per Person
View Trip
18 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

18 Days (17 Nights) Rome to Orlando
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 28 October 2026
Visit: Italy, Spain, Portugal, Puerto Rico, USA
Inside
$952
Oceanview
$1,267
Balcony
$1,505
Suite
$6,734
From
US$952
Per Person
View Trip
10 Day Bermuda & Caribbean Cruise: New York, Bermuda & St. Marteen with Azamara Cruises
Cruise
 (3)

10 Days (9 Nights) New York to San Juan
Cruise Line: Azamara Cruises
Ships: Azamara Journey, Azamara Quest
Departures: Oct 2026 to Oct 2027
Visit: USA, Bermuda, Saint Martin, Virgin Islands, Puerto Rico
Azamara Always Included
Inside
$1,609
Oceanview
$2,079
Balcony
$2,669
Suite
$4,629
From
US$1,609
Per Person
View Trip
9 Day Eastern Caribbean with Puerto Rico with Princess
Cruise
 (1)

9 Days (8 Nights) Fort Lauderdale to Fort Lauderdale
Cruise Line: Princess
Ship: Regal Princess
Departures: Oct 2026 to Feb 2027
Visit: USA, Saint Martin, Puerto Rico, Dominican Republic, Turks and Caicos Islands
Princess Standard
Inside
$699
Oceanview
-
Balcony
$954
Suite
$1,279
From
US$699
Per Person
View Trip
19 Day MSC Grand Voyages with MSC Cruises
Cruise
 (1)

19 Days (18 Nights) Genoa to Miami
Cruise Line: MSC Cruises
Ship: MSC Grandiosa
Departure: 26 October 2026
Visit: Italy, Spain, Portugal, Puerto Rico, USA
Inside
$1,051
Oceanview
$1,271
Balcony
$1,513
Suite
$3,249
From
US$1,051
Per Person
View Trip
8 Day Southern Caribbean Halloween Cruise with Virgin Voyages
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Virgin Voyages
Ship: Valiant Lady
Departure: 31 October 2026
Visit: Puerto Rico, Curacao, Aruba, Martinique, Saint Kitts and Nevis
Limited Time Offer
Inside
$1,137
Oceanview
$1,253
Balcony
$1,533
Suite
$4,053
From
US$1,137
Per Person
View Trip
8 Day Southern Caribbean Cruise with Royal Caribbean
Cruise
 (1)

8 Days (7 Nights) San Juan to San Juan
Cruise Line: Royal Caribbean
Ships: Grandeur of the Seas, Rhapsody of the Seas
Departures: May 2027 to Apr 2028
Visit: Puerto Rico, Virgin Islands, Sint Maarten, Saint Lucia, Barbados
Bonus Onboard Credit
Exclusive Savings
Inside
$689
Oceanview
$766
Balcony
$1,248
Suite
$1,398
From
US$689
Save 568
Per Person
View Trip
9 Day Baltimore To San Juan Cruise with Royal Caribbean
Cruise

9 Days (8 Nights) Baltimore to San Juan
Cruise Line: Royal Caribbean
Ship: Vision of the Seas
Departure: 21 October 2027
Visit: USA, Turks and Caicos Islands, Aruba, Curacao, Puerto Rico
Bonus Onboard Credit
Exclusive Savings
Inside
$646
Oceanview
$754
Balcony
$1,526
Suite
$2,046
From
US$646
Save 375
Per Person
View Trip
10 Day Boston To San Juan Cruise with Celebrity Cruises
Cruise

10 Days (9 Nights) Boston to San Juan
Cruise Line: Celebrity Cruises
Ship: Celebrity Summit
Departure: 20 October 2027
Visit: USA, Dominican Republic, Virgin Islands, Antigua and Barbuda, Puerto Rico
Exclusive Savings
Inside
$979
Oceanview
$1,029
Balcony
$1,204
Suite
$4,079
From
US$979
Save 551
Per Person
View Trip
8 Day Eastern Caribbean With Puerto Rico & Celebration Key with Princess
Cruise

8 Days (7 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Star Princess
Departures: Oct 2027 to Feb 2028
Visit: USA, Bahamas, Dominican Republic, Puerto Rico, Turks and Caicos Islands
Princess Standard
Sanctuary Collection
Inside
$749
Oceanview
$929
Balcony
$1,024
Suite
$1,399
From
US$749
Per Person
View Trip
15 Day Eastern/Western Caribbean Adventurer with Princess
Cruise

15 Days (14 Nights) Orlando to Orlando
Cruise Line: Princess
Ship: Caribbean Princess
Departures: Jul 2026 to Oct 2026
Visit: USA, Puerto Rico, Dominican Republic, Turks and Caicos Islands, Bahamas
Princess Standard
Inside
$966
Oceanview
$1,019
Balcony
$1,458
Suite
-
From
US$966
Per Person
View Trip
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